Ergot alkaloids are known lactation inhibitors and have recently been shown to inhibit prolactin-dependent mammary tumors in rats. Compounds of this type are therefore of interest as potential agents for the treatment of breast cancer. Studies on the biosynthesis of ergot alkaloids have progressed to the stage where the choice of compounds which may be invoked as intermediates has narrowed considerably. Further progress requires the synthesis of certain ergolines or potential precursors of this ring system. The objective of this project is to synthesize compounds in the ergoline series which will be tested as biosynthetic precursors in the ergot fungus and/or as potential mammary tumor inhibitors in rats. Approaches to these compounds will involve semisynthesis from naturally occurring alkaloids as well as attempts to develop a new total synthetic entry into the clavine series of ergot alkaloids.